3-Isobutyl-1-methylxanthine
Basic information
- CAS
28822-58-4- Standard SMILES
CC(C)Cn1c(=O)n(C)c(=O)c2[nH]cnc21- InChIKey
APIXJSLKIYYUKG-UHFFFAOYSA-N- Molecular formula
- C10H14N4O2
- Average molar mass
- 222.24 g/mol
- Monoisotopic mass
- 222.1116757
Overview
3-isobutyl-1-methyl-7H-xanthine is a 3-isobutyl-1-methylxanthine. It is functionally related to a 7H-xanthine. It is a tautomer of a 3-isobutyl-1-methyl-9H-xanthine.
Names & identifiers
- Preferred name
- 3-Isobutyl-1-methylxanthine
- IUPAC
- 1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
- English name
- 3-Isobutyl-1-methylxanthine
- Molecular formula
- C10H14N4O2
- Molecular weight
- 222.24
Names & synonyms
3-Isobutyl-1-methylxanthineIBMX28822-58-4isobutylmethylxanthine1-METHYL-3-ISOBUTYLXANTHINE3-Isobutyl-1-methyl-3,7-dihydro-1H-purine-2,6-dioneXanthine, 3-isobutyl-1-methyl-1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-3-(2-methylpropyl)-3-Isobutyl-1-methyxanthine3-isobutyl-1-methyl-7H-xanthine1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dioneSC 2964
Show more names
MIXIMXI5879-1GNSC 165960I5879-100MGI5879-250MGIBMX(NSC165960
SC-2964TBT296U68M1-methyl-3-(2-methylpropyl)-3,7-dihydro-1H-purine-2,6-dioneCHEBI:34795NSC-1659603 Isobutyl 1 methylxanthineDTXSID0040549Isobutyltheophylline
Database identifiers
- CAS
28822-58-4- PubChem CID
- 3758
- DTXSID
DTXSID0040549
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 69.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 318
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP1.22
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section147.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 200 · 200-201 °C(lit.)
- Boiling point
- 363.42 °C · 363.42°C (rough estimate)
- Density
- 1.2042 · 1.2042 (rough estimate)
- refractive index
- 1.65 · 1.6500 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- 1 M · DMSO: 1 M with gentle warming
- form
- powder
- pka
- 8.61 · 8.61±0.70(Predicted)
- color
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 70 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- rtecs
- ZD8500000
- hs_code
- 29335990
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312a-P330-P501a
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationCompounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases.
Applications
DescriptionIBMX (28822-58-4) is a pan-specific inhibitor of phosphodiesterases (IC50=2-50 μM). Inhibition of PDEs leads to increased concentration of intracellular cAMP which activates PKA.2IBMX does not inhibit PDE8 or PDE9.3Weak adenosine receptor antagonist.4
UsesA nonspecific inhibitor of phosphodiesterases
Usesphosphodiesterase inhibitor
Uses3-Isobutyl-1-methylxanthine is used in inhibition of phenylephrine-induced release of 5-hydroxytryptamine from neuroendocrine epithelial cells of the airway mucosa (IC50 = 1.3 uM). Also inhibits ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. Inhibits the growth of carcinoma cells both in vivo and in vitro in mice.
General Description3-isobutyl-1-methylxanthine/IBMX is a non-selective, non-specific inhibitor of cAMP and cGMP phosphodiesterases. IBMX can induce melanogenesis, and can be used as a positive control in melanogenesis research. In oocyte research, IBMX assists in maintaining the germinal vesicle (GV) arrest of prophase I oocytes.
Additional notes
DefinitionChEBI: 3-isobutyl-1-methyl-9H-xanthine is a 3-isobutyl-1-methylxanthine. It is functionally related to a 9H-xanthine. It is a tautomer of a 3-isobutyl-1-methyl-7H-xanthine.
Related reactions
7 records
Compound notes
Loading…